Methanol → 1-Propanone, 3-(4-aminophenyl)-1-phenyl-

HRID 356470Notes

Reaction equation

HRID 356470 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])=[CH:6][CH:5]=1)([O-])=O.CO.[H][H]>[Ni].C1COCC1>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:13])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 146543-(4-Nitrophenyl)-1-phenylprop-2-en-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 122630371-Propanone, 3-(4-aminophenyl)-1-phenyl-

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(4-nitro-phenyl)-1-phenyl-prop-2-en-1-one (24.9 g, 98.3 mmol), Raney nickel (7.0 g), MeOH (100 mL), and THF (400 mL) was shaken in a hydrogen atmosphere of 51 psi at 20° C. for 18.5 hours. The catalyst was filtered, and the filtrate was concentrated. The residue was recrystallized from 95% EtOH, to give the title compound, m.p. 76°-78° C. 1H NMR (CDCl3) δ 2.98 (t, 2 H), 3.25 (t, 2 H), 3.62 (bs, 2 H), 6.65 (d, 2 H), 7.05 (d, 2 H), 7.40-7.61 (m, 3 H), 7.96 (d, 2 H).

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was recrystallized from 95% EtOH

Sources & evidence

ORD record
ord-5e9fcdfed4ea4e5a95204807ffb6e720
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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